Showing Compound Succinic acid (FDB001931)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:10 UTC

Update date

2019-11-26 02:56:46 UTC

Primary ID

FDB001931

Secondary Accession Numbers

FDB031187

Chemical Information

FooDB Name

Succinic acid

Description

Succinic acid, also known as ethylenesuccinate or butanedionic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Succinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Succinic acid exists in all living species, ranging from bacteria to humans. Succinic acid is an odorless and sour tasting compound. Succinic acid is found, on average, in the highest concentration within a few different foods, such as star fruits, milk (cow), and mexican groundcherries. Succinic acid has also been detected, but not quantified in, several different foods, such as macadamia nut (m. tetraphylla), beech nuts, mung beans, rubus (blackberry, raspberry), and grapefruit/pummelo hybrids. This could make succinic acid a potential biomarker for the consumption of these foods. Succinic acid is a potentially toxic compound.

CAS Number

110-15-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2-Ethanedicarboxylic acid	ChEBI
Acide butanedioique	ChEBI
Acide succinique	ChEBI
Acidum succinicum	ChEBI
Amber acid	ChEBI
Asuccin	ChEBI
Bernsteinsaeure	ChEBI
Butandisaeure	ChEBI
Butanedionic acid	ChEBI
Dihydrofumaric acid	ChEBI
e363	ChEBI
Ethylenesuccinic acid	ChEBI
HOOC-CH2-CH2-COOH	ChEBI
Spirit OF amber	ChEBI
1,2-Ethanedicarboxylate	Generator
Butanedionate	Generator
Dihydrofumarate	Generator
Ethylenesuccinate	Generator
Succinate	Generator
2-Acetamido-2-deoxy-D-glucose	HMDB
D-GlcNAc	HMDB
N-Acetyl-D-glucosamine	HMDB
N-Acetylchitosamine	HMDB
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxy D glucose	HMDB
2 Acetamido 2 deoxyglucose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
Acetylglucosamine	HMDB
1,4-Butanedioate	HMDB
1,4-Butanedioic acid	HMDB
Katasuccin	HMDB
Wormwood acid	HMDB
1,2 Ethanedicarboxylic acid	HMDB
1,4 Butanedioic acid	HMDB
Potassium succinate	HMDB
Succinate, ammonium	HMDB
Butanedioic acid	HMDB
Succinate, potassium	HMDB
Ammonium succinate	HMDB
1,4-BUTANEDIOIC ACID (SUCCINIC ACID)	biospider
1cze	biospider
Acid of amber	biospider
Amber acid, butanedioic acid, ethylenesuccinic acid	biospider
Butanedioic acid (9CI)	biospider
Butanedioic acid diammonium salt	biospider
Butanedioic acid, 9CI	db_source
E363	db_source
Ethane-1,2-dicarboxylic acid	db_source
Ethanedicarboxylic acid	biospider
Ethylene dicarboxylic acid	biospider
Ethylene succinic acid	biospider
FMR	biospider
MAE	biospider
Sal succini	biospider
Salt of amber	biospider
SIN	biospider
Spirit of amber	biospider
SUC	biospider
SUCC	biospider
succinate, 9	biospider
Succinellite	biospider
Succinic acid (8CI)	biospider
Succinic acid, acs	biospider
Succinicum acidum	biospider
Succinicun acidum	biospider
Wormwood	biospider

Predicted Properties

Property	Value	Source
Water Solubility	211 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-0.4	ChemAxon
logS	0.25	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	23.54 m³·mol⁻¹	ChemAxon
Polarizability	10.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C4H6O4

IUPAC name

butanedioic acid

InChI Identifier

InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

InChI Key

KDYFGRWQOYBRFD-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCC(O)=O

Average Molecular Weight

118.088

Monoisotopic Molecular Weight

118.02660868

Classification

Description

belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:15741 )
alpha,omega-dicarboxylic acid (CHEBI:15741 )
Dicarboxylic acids (LMFA01170043 )

Ontology

Gastrointestinal disorders:

Diarrhea

Cardiac disorders:

Cardiomyopathy

Cancer:

Lung cancer

Ingestion

Trace element

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.68%; H 5.12%; O 54.19%	DFC
Melting Point	Mp 184-185°	DFC
Boiling Point	Bp 235° dec.	DFC
Experimental Water Solubility	83.2 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	-0.59	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 5.7 (25°, H2O)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-0920000000-f286e6204a4163b823ba	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-bf336910bb37d7f78140	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-9800000000-df5ff4e8457d2d4ef919	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00c1-3930000000-3cc18e719822b5af661a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-93b4807ae6275a3e59d7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kos-9100000000-f1df0903a24c305e68ec	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0910000000-300c33b39fb991b5a73e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-f286e6204a4163b823ba	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-bf336910bb37d7f78140	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9800000000-df5ff4e8457d2d4ef919	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00c1-3930000000-3cc18e719822b5af661a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-f838d863ee7c2b111f02	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-9300000000-f0644daf4fbb11fcc2dc	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-9710000000-ff8325384b9eefd19106	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9300000000-f9dc864d93a09d3074f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9300000000-76c151de384928b2256f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-01b9-7900000000-51d2341c097f04827944	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-004i-9000000000-93b4807ae6275a3e59d7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03dj-0971010000-37d214dc7a8fdc26116b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-249222ac742c1634cec9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-9000000000-6897d49472dba6a34a27	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0490000000-d138f8023125921b4b82	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-1900000000-4ffdabe5bde527b66982	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9100000000-c20baa818f5ff5f678c1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-7a49a18aa6fcb2540a12	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-9955aeb0e5a9f88ae70e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00di-9000000000-7e1f195f111b4eafb4fa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00xr-9400000000-e50afc90e20cd420ba9b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00xr-9600000000-43167f2549cbb5d5f7e8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-4ffdabe5bde527b66982	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9100000000-7a8bfa543dc087bea06d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-fdec6c7458176f3cbeb8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-9955aeb0e5a9f88ae70e	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-2900000000-9d959a53833b07094158	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0l6r-9600000000-c367e11e737714d41418	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-e65aa602a8293debec36	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-e1f840494c9003279869	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-7900000000-1089efd4a3469bcf14f1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0604-9000000000-0e0e60bb202ffb004894	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-05di-9100000000-c629bea41d0d3d896425	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15741

Phenol-Explorer ID

Not Available

DrugBank ID

DB00139

HMDB ID

HMDB00254

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1040431

SuperScent ID

1110

Wikipedia ID

Succinic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
additive	64047	Any substance which is added to food to preserve or enhance its flavour and/or appearance.	DUKE
anti feedant			DUKE
bruchiphobe			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
dye	37958		DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sour	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Succinic acid (FDB001931)

Structure for FDB001931 (Succinic acid)